JPS59225135A - Ether derivative, its preparation, and insecticide and acaricide comprising it as active ingredient - Google Patents

Ether derivative, its preparation, and insecticide and acaricide comprising it as active ingredient

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Publication number
JPS59225135A
JPS59225135A JP58101245A JP10124583A JPS59225135A JP S59225135 A JPS59225135 A JP S59225135A JP 58101245 A JP58101245 A JP 58101245A JP 10124583 A JP10124583 A JP 10124583A JP S59225135 A JPS59225135 A JP S59225135A
Authority
JP
Japan
Prior art keywords
group
atom
formula
general formula
hydrogen atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP58101245A
Other languages
Japanese (ja)
Other versions
JPH042578B2 (en
Inventor
Hiroshi Kishida
博 岸田
Toshihiko Yano
俊彦 矢野
Masachika Hirano
平野　雅親
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP58101245A priority Critical patent/JPS59225135A/en
Publication of JPS59225135A publication Critical patent/JPS59225135A/en
Publication of JPH042578B2 publication Critical patent/JPH042578B2/ja
Granted legal-status Critical Current

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Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

NEW MATERIAL:An ether derivative shown by the formula I [R1 and R<2> are H, halogen, alkyl, alkoxyl, haloalkyl, nitrile, nitro, etc., or R1 and R2 are linked to form 5- or 6-membered ring (may contain O, or S); R3 and R4 are methyl, or ethyl, or R3 and R4 are linked to form ethylene; X is O, or methylene; Y is group shown by the formula II, or formula III (R<5> is H, or F; R6 is H, halogen, or alkyl; Q is N, or methine; Z is O, S, imino, etc.)]. USE:An insecticide and acaricide. Having high and immediate effects, low toxicity, extremely effective against insect pests having resistance to organic phosphorous and carbamate agents. PREPARATION:For example, a compound shown by the formula V is reacted with a compound shown by the formula Y-CH2-A1 (A1 is h halogen, etc.) in the presence of a deoxidizer to give a compound shown by the formula I .

Description

【発明の詳細な説明】 本発明は下記一般式（１）で示されるエーテル誘導体、
その製造法およびそれを有効成分として含有する殺虫、
殺ダニ剤に関する。Detailed Description of the Invention The present invention relates to an ether derivative represented by the following general formula (1),
its production method and insecticides containing it as an active ingredient;
Regarding acaricides.

、ａＢ Ｒａ 〔式中、Ｒ１および几２は同一または相異なり、水素原
子、ハロゲン原子、低級アルキル基、低級アルコキシル
基、低級ハロアルキル基、低級ハロアルコキシルＭ、低
級アルキル基オ基、ニトリル基またはニトロ基を表わし
、さらに、Ｒ１とＲ２とが末端で結合し、１〜２個の酸
素原子または硫黄原子を環内に含んでいてもよい飽和ま
たは不飽和の５員環もしくは６貝環を形成することもで
きる。, aB Ra [wherein R1 and 几2 are the same or different, hydrogen atom, halogen atom, lower alkyl group, lower alkoxyl group, lower haloalkyl group, lower haloalkoxyl M, lower alkyl group, nitrile group or nitro R1 and R2 are bonded at their terminals to form a saturated or unsaturated 5-membered or 6-shell ring that may contain 1 to 2 oxygen atoms or sulfur atoms in the ring. You can also do that.

損およびＲ４は同一または相異なり、メチル基またはエ
チル基を表わすか、またはＲ８とＲ４が末端で結合しエ
チレン基を表わす。and R4 are the same or different and represent a methyl group or an ethyl group, or R8 and R4 are bonded at the terminal to represent an ethylene group.

Ｘは酸素原子または　メチレン基を表わし、Ｙは　式 または一般式 で示される基（ここで、Ｒ５は水素原子またはフッ素原
子を表わし、Ｒ６は水素原子、ハロゲン原子または低級
アルキル基を表わす。Ｑは窒素原子またはメチン基を表
わし、２は酸素原子、硫黄原子、イミノ基またはメチレ
ン基を表わす。）を表わす。〕 本発明者らは、優れた殺虫、殺ダニ剤を開発すべく数多
くの研究を行なった結果、上記一般式（Ｉ）で示される
エーテル誘導体が１．殺虫、殺ダニ効力が高く、かつ速
効的である。　２１人畜に低毒である。　３．有機リン
剤あるいはカーバメート剤抵抗性の害虫に対しても卓効
を発揮する。X represents an oxygen atom or a methylene group, and Y represents a group represented by the formula or general formula (where R5 represents a hydrogen atom or a fluorine atom, and R6 represents a hydrogen atom, a halogen atom, or a lower alkyl group. represents a nitrogen atom or a methine group, and 2 represents an oxygen atom, a sulfur atom, an imino group or a methylene group). ] The present inventors conducted numerous studies to develop excellent insecticides and acaricides, and as a result, the ether derivative represented by the above general formula (I) was found to be 1. It has high insecticidal and acaricidal efficacy and is fast-acting. 21 Low toxicity to humans and animals. 3. It is also highly effective against pests that are resistant to organic phosphorus agents or carbamate agents.

４、比較的安価に製造できる。4. Can be manufactured relatively inexpensively.

などの優れた性質を有することを見出し、本発明を完成
するに至った。The present inventors have discovered that it has excellent properties such as, and have completed the present invention.

本発明化合物が特に有効な具体的な害虫としては、ウン
カ類、ヨコバイ類、アブラムシ類、カメムシ類などの半
翅目、コナガ、ニカメイガ、ヨトウ類などの鱗翅目、ア
カイエカ、イエバエなどの双翅目、チャバネゴキブリな
どの網翅目、その他鞘翅目、直翅目およびハダニ類とし
て、ニセナミハダニ、ミカノハダニなどが挙げられる。Specific pest insects for which the compounds of the present invention are particularly effective include Hemiptera such as planthoppers, leafhoppers, aphids, and stink bugs; Lepidoptera such as diamondback moths, Japanese mealybugs, and armyworms; and Diptera such as Culex mosquitoes and houseflies. , the German cockroach and other orders of the order Orthoptera, other order orders of the order Coleoptera, orders of the Orthoptera, and spider mites include the Japanese spider mite, the red spider mite, and the like.

一般式（Ｉ）で示される本発明化合物は次の方法により
製造することができる。The compound of the present invention represented by general formula (I) can be produced by the following method.

（製造法人） 一般式（Ｉ［） １１ ４ 〔式中、ｌＬｒ　、　Ｒ２、Ｒｓ　、且４およびＸは前
述と同じ意味を有する。］ で示されるアルコール化合物と一般式（Ｉｌｌ）Ｙ　−
ＣＨ２−Ａ　ｔ　　　　　　　　（２））〔式中、Ｙは
前述と同じ意味を有し、Ａｌはハロゲン原子、トシルオ
キシ基まｔこはメシルオキシ基を表わす。〕 で示される化合物とを脱酸剤の存在丁番こ反応させる方
法。(Manufacturing corporation) General formula (I[) 11 4 [Wherein, 1Lr, R2, Rs, and 4 and X have the same meanings as above. ] An alcohol compound represented by the general formula (Ill) Y −
CH2-A t (2)) [wherein, Y has the same meaning as above, Al represents a halogen atom, a tosyloxy group or a mesyloxy group. ] A method of reacting the compound shown in the following in the presence of a deoxidizing agent.

（製造法Ｂ） 一般式（１ｖ） ８ ４ 〔式中、Ｒ１，Ｒ２、Ｒａ　、　ｌＬ４およびＸζよ前
述と同じ意味を有し、Ａ２は）１０ゲン原子、トシルオ
キシ基またはメジフレオキシ基を表わす。〕 で示される化合物と一般式（ｖ） Ｙ−ＣＨ２−ＯＲ（ｖ） し式中、Ｙは前述と同じ意味を有する。］で示されるア
ルコール化合物とを脱酸剤の存在下に反応させる方法。(Production method B) General formula (1v) 8 4 [In the formula, R1, R2, Ra, 1L4 and Xζ have the same meanings as above, and A2 represents a 10-gen atom, a tosyloxy group or a medifuroxy group. ] A compound represented by the general formula (v) Y-CH2-OR(v) In the formula, Y has the same meaning as above. ] in the presence of a deoxidizing agent.

（製造法Ｃ） 一般式（ＶｉＪ ［式中、ｌｔｘおよびＲ２は前述と同じ意味を有７゛る
。］ で示されるフェノール誘導体と一般式（４）％式％（ 〔式中、Ｒａ　、几４およびＹは前述と同じ意味を有し
、Ａ８はハロゲン原子、トシルオキシ基またはメシルオ
キシ基を表わす。〕で示される化合物とを脱酸剤の存在
下に反応させる方法。(Production method C) A phenol derivative represented by the general formula (ViJ [wherein, ltx and R2 have the same meanings as above] and a phenol derivative represented by the general formula (4)% formula% ([wherein, Ra, 几4 and Y have the same meanings as above, and A8 represents a halogen atom, a tosyloxy group, or a mesyloxy group.] in the presence of a deoxidizing agent.

前記製造法Ａ、ＢおよびＣにおいて、脱酸剤としては、
例えばアルカリ金属、アルカリ金属水素化物、アルカリ
金属アミド、アルカリ金属水酸化物、アルカリ金属炭酸
塩などのアルカリ金属出来の塩基、トリエチルアミン、
ｌ、８−ジアザヒシクロ［５，４，０］−７−ウンデセ
ンなどの有機塩基などを挙げることができる。In the production methods A, B and C, the deoxidizing agent is
For example, alkali metals, alkali metal hydrides, alkali metal amides, alkali metal hydroxides, alkali metal bases such as alkali metal carbonates, triethylamine,
Examples include organic bases such as 1,8-diazahicyclo[5,4,0]-7-undecene.

これらの塩基は、他の反応試剤と共にそのまま反応に倶
してもよいが、アルカリ金屑由来の塩基を用いる時は予
め、該塩基と一般式（［）　、　（Ｖ）または（旬で示
されるアルコール化合物またはフェノール誘導体とを反
応させ、夫々一般式（■′）、（ｖつまたは（■′）で
示されるアルカリ金属誘導体に導いた後、夫々前記−・
般式佃）、（Ｆｔ’）または（４）で示される化合物と
反応させることに。１こり、目的物を得ることもできる
。These bases may be directly involved in the reaction together with other reaction reagents, but when using a base derived from alkali metal scrap, it is necessary to combine the base with the general formula ([), (V) or (shown by After reacting with an alcohol compound or a phenol derivative to lead to an alkali metal derivative represented by the general formula (■'), (v or (■'), respectively, the above-mentioned -.
To react with a compound represented by the general formula Tsukuda), (Ft') or (4). You can also get the desired object in one click.

凡８ 几４ Ｙ　−０ｆｉ２−　Ｕ−Δｉ　　　　　　　　　（ｖ’
）〔式中、損、Ｒ２，几８．良、ＸおよびＹは前述と同
じ意味を有し、Ｍはアルカリ金属原子を表わす。」 これらの製造法において反応詰媒は必須ではないが、反
応をより円滑に進行させるために不活性溶媒を用いるこ
とが好Ｊ二しく、そのような溶媒としては例えばジメチ
ルホルムアミド、ジメヂルンルポキシト、テトラヒドロ
フラン、ジメトキシエタン、トルエン、水などおよびそ
れらの混合劇媒を挙げることができ、溶媒として水ヲ用
いる時は、ベンジ？レトリエチルアンモニウムクロリド
、テトラ−ｎ−ソチルアンモニウＭの相聞移動触媒を用
いることにより、効率よく反応させることができる。8 几4 Y −0fi2− U−Δi (v'
) [In the formula, loss, R2, 几8. Good, X and Y have the same meanings as above, and M represents an alkali metal atom. Although a reaction packing medium is not essential in these production methods, it is preferable to use an inert solvent in order to make the reaction proceed more smoothly. Examples of such solvents include dimethylformamide, dimedylneolupoxy, etc. Examples of solvents include tetrahydrofuran, dimethoxyethane, toluene, water, and mixtures thereof. When water is used as a solvent, benzene, By using a phase transfer catalyst of retriethylammonium chloride and tetra-n-sotylammonium M, the reaction can be carried out efficiently.

また、これらの製造法において反応温度は、特に制限さ
れるものではないが、通常−３０℃から反応混合物のｄ
ｉＩ点までの温度であり、通常室温から２００°Ｃの範
囲である。In addition, the reaction temperature in these production methods is not particularly limited, but is usually from -30°C to d of the reaction mixture.
The temperature is up to the iI point, and is usually in the range from room temperature to 200°C.

反応時門は反応条件によっても変わり得るが、通常０．
５〜５０時間である。The reaction time may vary depending on the reaction conditions, but is usually 0.
It is 5 to 50 hours.

製造法人において、一般式（ＩＩ）で示されるアルコー
ル化合物と一般式（２）で示される化合物のモル比は通
常１：０．１〜ＩＯであり、好ましくはｌ：１〜１．２
であり、また、該アルコール化合ｙＪ 物と脱酸剤のモル比は１１〜１０の範囲、通σ、？ 常は１：＄ｔ〜２である。In the manufacturing corporation, the molar ratio of the alcohol compound represented by general formula (II) to the compound represented by general formula (2) is usually 1:0.1 to IO, preferably 1:1 to 1.2.
, and the molar ratio of the alcohol compound yJ to the deoxidizing agent is in the range of 11 to 10, with σ, ? Usually the ratio is 1:$t~2.

製造法Ｂにおいて一般式（１’／）で示される化合物と
一般式（Ｖ）で示されるアルコール化合物のモル比は通
常１：０．２〜５であり、好ましくは１：製造法Ｃにお
いて一般式（■）で示されるフェノール誘導体と一般式
（４）で示される化合物のモル比は通常１：０．１〜１
ｏであり、好ましくはｌ：０．８〜１であり、該フェノ
ール誘導体と脱酸０．３ 剤のモル比は１：◆〜１ｏの範囲、ζＷ千君ヨーリＩＩ
爾瑠１通常は１ニー〜２である。In production method B, the molar ratio of the compound represented by general formula (1'/) and the alcohol compound represented by general formula (V) is usually 1:0.2 to 5, preferably 1:general in manufacturing method C. The molar ratio of the phenol derivative represented by formula (■) and the compound represented by general formula (4) is usually 1:0.1 to 1.
o, preferably l:0.8-1, the molar ratio of the phenol derivative and the deoxidizing agent is in the range of 1:◆-1o, ζW Senkun Yori II
Erru 1 Usually 1 knee to 2.

上記のような製造法により得られる本発明化合物は、必
要に応じて、蒸留、カラムクロマトグラフィーなどの手
段により精製することができる。The compound of the present invention obtained by the above production method can be purified by means such as distillation and column chromatography, if necessary.

前記一般式（１）で示される本発明化合物におい原子が
挙げられ、低級アルキル基としては、例えばメチル基、
エチル基、ｎ−プロピル基、ｉｓ。Examples of the odor atoms of the compound of the present invention represented by the general formula (1) include lower alkyl groups, such as methyl groups,
Ethyl group, n-propyl group, is.

−プロピル基が挙げられ、低級アルコキシル基としては
、例えばメトキシ基が挙げられ、低級ハロアルキル基と
しては、例えばトリフルオロメチル基が挙げられ、低級
ハロアルコキシル基としては、例えばジフルオロメトキ
シ基、トリフルオロメト千シ基が挙げられ、低級アルキ
ルチオ基としては、例えばメチルチオ基が挙げられる。Examples of the lower alkoxyl group include a methoxy group, examples of the lower haloalkyl group include a trifluoromethyl group, and examples of the lower haloalkoxyl group include a difluoromethoxy group and a trifluoromethyl group. Examples of the lower alkylthio group include methylthio.

また、几ｌとｆｔ２とが末端で結合し、１〜２個の酸素
原子または硫黄原子を環内に含んでいてもよい飽和また
は不飽和の５員環もしくは６員環を形成する場合として
は、一般式 キシフェニル基、８．４−ジ≠雫ロメチレンジオキシフ
ェニルｉ、５，６．７．８−テトラヒドロ−β−ナフチ
ル基、５−インダニル基、２゜８−ジヒドロベンゾフラ
ン−５−イルＭ、２゜８−ジヒドロベンゾフラン−６一
イルＭ、２゜８−ジヒドロベンゾチオフェン−５−イル
基および２，８−ジヒドロベンゾチオフェン−６−イル
基を表わす場合を挙げることができる。In addition, when 几l and ft2 are bonded at the terminal to form a saturated or unsaturated 5-membered or 6-membered ring that may contain 1 to 2 oxygen atoms or sulfur atoms in the ring, , general formula xyphenyl group, 8.4-di≠dropromethylenedioxyphenyl i, 5,6.7.8-tetrahydro-β-naphthyl group, 5-indanyl group, 2゜8-dihydrobenzofuran-5-yl M, 2°8-dihydrobenzofuran-6-yl M, 2°8-dihydrobenzothiophen-5-yl group and 2,8-dihydrobenzothiophen-6-yl group can be mentioned.

また、置換基Ｒｓにおけるハロゲン原子としては、フッ
素原子、塩素原子、臭素原子およびヨウ素原子が挙げら
れ、低級アルキル基としては、例えばメチル基、エチル
基、ｎ−プロピル基、１ｓｏ−プロピル基が挙げられる
。Further, examples of the halogen atom in the substituent Rs include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and examples of the lower alkyl group include a methyl group, an ethyl group, an n-propyl group, and a 1so-propyl group. It will be done.

尚、本発明化合物において、置換基Ｒ８および栴が夫々
異なる基を表わす場合には、光学異性体が存在し得るが
、本発明はこれらの光学異性体およびその混合物をも含
むものである。In the compound of the present invention, when the substituent R8 and the substituent R8 represent different groups, optical isomers may exist, and the present invention also includes these optical isomers and mixtures thereof.

次に製造例を示す。Next, a manufacturing example will be shown.

製造例１　製造法人による化合物（１）の合成無水ジメ
チルスルホキシドｌＯ艷に水素化ナトリウム（６２％オ
イルサスペンシコン）０、１９９　（５，Ｑ　ｒｒｎｎ
ｏｌ）を加え、次いで２．２−ジメチル−５−（４−ト
リルオキシ）プロパ／　−＃　０．９７　Ｆ　（５，Ｑ
ｍｍｏｌ　）の無水ジメチルスルホキシド溶液５−を１
０分間で滴下した後、６５〜７０°Ｃで１時間撹拌した
。室温まで冷却後、３−フェノキシベンジルプロミド１
．８２１　（５，Ｑｍｍｏｌ　）（１）無水’）　）　
チア１／　スルホキシド溶液５　ｍｅを１０分間で滴下
した後、室温下に１ｒｓ３ｆｆｌ拌した。反応混合物を
水１００ｄに注ぎ、トルエン３０−で２回抽出し、水洗
後無水硫酸ナトリウムで乾燥後、トルエンを留去し、シ
リカゲルを用いたカラムクロマトグラフィーにより精製
し１．目的とする後記化合物（１）　１．６８１を無色
透明液体として得た（収率８６．６％、１１Ｄ　　１．
５５７９）。Production Example 1 Synthesis of Compound (1) by Manufacturing Corporation Sodium hydride (62% oil suspension) 0.199 (5,Q rrnn)
ol) and then 2,2-dimethyl-5-(4-tolyloxy)prop/-# 0.97 F (5,Q
mmol) of anhydrous dimethyl sulfoxide solution to 1
After dropping for 0 minutes, the mixture was stirred at 65-70°C for 1 hour. After cooling to room temperature, 3-phenoxybenzyl bromide 1
．． 821 (5, Qmmol) (1) Anhydrous'))
After dropping 5 me of thia 1/sulfoxide solution over 10 minutes, the mixture was stirred at room temperature for 1rs3ffl. The reaction mixture was poured into 100 d of water, extracted twice with 30 g of toluene, washed with water, dried over anhydrous sodium sulfate, distilled off the toluene, and purified by column chromatography using silica gel. The desired compound (1) 1.681 described later was obtained as a colorless transparent liquid (yield 86.6%, 11D 1.
5579).

製造例２　製造法Ｂによる化合物（４）の合成無水ジメ
チルスルホキシド１０ｍ７！に水素化ナトリウム（６２
％オイルサスペンション）０、　ｌ　９　ｆ　（５，Ｑ
ｍｍｏｌ　）を加え、次いで８−フェノキシベンジルア
ルコール１．００　ｆ　（５，Ｑｍｍｏｌ）の無水ジメ
チルスルホキシド溶液５−を加えた後、６５〜７０°Ｃ
で１時間攪拌した。Production Example 2 Synthesis of Compound (4) by Production Method B 10m7 of anhydrous dimethyl sulfoxide! Sodium hydride (62
% oil suspension) 0, l 9 f (5, Q
65-70 °C
The mixture was stirred for 1 hour.

室温まで冷却後、２．２−ジメチル−１−（４−）＃ロ
フエノキシ）−３−トシルオキシプロパン１．７６１　
（５，０ｍｍｏＩ　）の無水ジメチルスルホキシド溶液
５ゴを１０分間で滴下シタ後、１８０〜１４０°Ｃで７
時間攪拌した。After cooling to room temperature, 2.2-dimethyl-1-(4-)#lophenoxy)-3-tosyloxypropane 1.761
(5.0 mmol) of anhydrous dimethyl sulfoxide solution was added dropwise for 10 minutes, and then heated to 180-140°C for 7 hours.
Stir for hours.

室温まで冷却後、反応混合物を水１００　ｍｌに注ぎ、
トルエン８０−で２回抽出し、水洗後、無水硫酸ナトリ
ウムで乾燥後、トルエンを留去し、シリカゲルを用いた
カラムクロマトクーラフィーにより精製し、目的とする
後記化合物（４）　０．６２１を無色透明液体として得
た（収率３２．６％、ｎＤｌ、５５０８）。After cooling to room temperature, the reaction mixture was poured into 100 ml of water,
Extracted twice with 80% of toluene, washed with water, dried over anhydrous sodium sulfate, distilled off the toluene, and purified by column chromatography using silica gel to obtain the desired compound (4) 0.621 as a colorless product. Obtained as a clear liquid (yield 32.6%, nDl, 5508).

製造例８　製造法Ｃによる化合物（４０）の合成無水ジ
メチルスルホキシド１０ｍ／、水素化ナトリウム（６２
％オイルサスベンジぢン）０．０８８１　（２，２９ｍ
ｍｏｌ）、４−フルオｏフェノール０．２５７９　（２
，２９ｍｍｏｌ）　　および２゜２−ジメチル−１−（
４−フルオロ−８−フェノキシベンジルオキシ）−８−
トシルオキシプロパン１．００９　（２，１８ｒｎｍｏ
ｊ　）　（Ｄ混合物を１８０〜１４０°Ｃで６時間攪拌
した。室温まで冷却後、反応混合物を水１００−に注ぎ
、トルエン８０−で２回抽出し、水洗後、無水硫酸ナト
リウムで乾燥後、トルエンを留去し、シリカゲルを用い
たカラムクロマトグラフィ６２．７％、ｎ　Ｄｌ−５４
１７）。Production Example 8 Synthesis of Compound (40) by Production Method C 10 m/m of anhydrous dimethyl sulfoxide, 62
% oil suspension) 0.0881 (2,29m
mol), 4-fluorophenol 0.2579 (2
, 29 mmol) and 2゜2-dimethyl-1-(
4-Fluoro-8-phenoxybenzyloxy)-8-
Tosyloxypropane 1.009 (2,18rnmo
j) (The mixture D was stirred at 180 to 140 °C for 6 hours. After cooling to room temperature, the reaction mixture was poured into 100 °C of water, extracted twice with 80 °C of toluene, washed with water, and dried over anhydrous sodium sulfate. Distill toluene and column chromatography using silica gel 62.7%, n Dl-54
17).

次にこれらの製造例に示した製造法に準じて製造した本
発明化ａ物のいくつかを表１に示す。Next, Table 1 shows some of the compounds of the present invention a produced according to the production methods shown in these production examples.

表　　ｌ ｓ ※　上記一般式（Ｉ）で示される化合物の置換基Ｒｒ　
、　Ｒ２、凡１１．Ｒ４，ＸおよびＹの内容。Table l s * Substituents Rr of the compound represented by the above general formula (I)
, R2, about 11. Contents of R4, X and Y.

本発明化合物を殺虫、殺ダニ剤の有効成分として用いる
場合は、通常、固体担体、成体担体、ガス状担体あるい
はその他の製剤用補助剤（例えば界面活性剤、分散剤、
湿展剤、安定剤等）と混合して各種の製剤、例えば乳剤
、水和剤、粉剤、粒剤、油剤、エアゾール、加熱燻蒸剤
（蚊取線香、電気蚊取等）、フオソギング等の煙霧剤、
非加熱燻蒸剤、毒餌等にする。When the compound of the present invention is used as an active ingredient of an insecticide or acaricide, it is usually a solid carrier, an adult carrier, a gaseous carrier, or other formulation auxiliary agents (such as surfactants, dispersants, etc.).
Wetting agents, stabilizers, etc.) to produce various preparations, such as emulsions, wettable powders, powders, granules, oils, aerosols, heated fumigants (mosquito coils, electric mosquito repellents, etc.), fumes such as fusogging, etc. agent,
Use non-heated fumigant, poison bait, etc.

これらの製剤中の有効成分含危は０．１％〜９５％であ
る。The active ingredient content in these formulations is 0.1% to 95%.

固体担体としては粘土類（例えばカオリン、ベントナイ
ト、酸性白土、ピロフィライト、セリサイト）、タルク
類、その他無機鉱物（たとえば水和二酸化ケイ素、軽石
、珪藻土、硫黄粉末、活性炭）などの微粉末ないし粉状
物が挙げられる。Solid carriers include fine powders or powders such as clays (e.g. kaolin, bentonite, acid clay, pyrophyllite, sericite), talcs, and other inorganic minerals (e.g. hydrated silicon dioxide, pumice, diatomaceous earth, sulfur powder, activated carbon). Things can be mentioned.

また液体担体としてはアルコール類（例えばメチルアル
コール）、ケトン類（例えばアセトン、メチルエチルケ
トン）、エーテルＭ（例、ｔばエチルエーテル、ジオキ
サン、セロソルブ、テトラヒドロフラン）、芳香族炭化
水累類（例えばベンゼン、トルエン、キシレン、メチル
ナフタレン）、脂肪族炭化水素類（例えばケロシン、灯
油）、エステル類、ニトリル類、酸アミド類Ｃ例えばジ
メチルホルムアミド、ジメチルア士ドアミド）、ハロゲ
ン化炭化水素（例えばジクロロエタン、トリクロロエチ
レン、四塩化炭素）などがあげられる。Liquid carriers include alcohols (e.g. methyl alcohol), ketones (e.g. acetone, methyl ethyl ketone), ethers (e.g. ethyl ether, dioxane, cellosolve, tetrahydrofuran), aromatic hydrocarbons (e.g. benzene, toluene). , xylene, methylnaphthalene), aliphatic hydrocarbons (e.g. kerosene, kerosene), esters, nitriles, acid amides (e.g. dimethylformamide, dimethylamide), halogenated hydrocarbons (e.g. dichloroethane, trichloroethylene, tetrachloride) carbon), etc.

また、界面活性剤としてはアルキル硫酸エステル類、ア
ルキルスルホン酸塩、アルキルアリ−ルスＪｌ／　ボン
酸塩、ポリエチレングリコールエーテル類、多価アルコ
ールエステル類などが挙げられる。Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkylaryl esters, polyethylene glycol ethers, and polyhydric alcohol esters.

さらに、使用できる固着剤や分散剤としてはカゼイン、
ゼラチン、でんぷん粉、ＯＭＧ、アラヒアゴム、アルギ
ン酸、リクニンスルフォネート、ベントナイト、糖蜜、
ポリヒニルアルコール、松根油、寒天などがあり、安定
剤としては例えばＰＡＰ　（リン酸イソプロピル）、Ｔ
ＣＰ（トリクレジルホスフェート）　、ｈ−ル油、ｘボ
キシ化油、各種界面活性剤、各油脂肪酸またはそのエス
テルなどがあげられる。In addition, casein, fixing agents and dispersants that can be used include
Gelatin, starch powder, OMG, arahia gum, alginic acid, licunin sulfonate, bentonite, molasses,
Examples of stabilizers include polyhinyl alcohol, pine oil, agar, and stabilizers such as PAP (isopropyl phosphate) and T.
Examples include CP (tricresyl phosphate), h-ru oil, x-boxylated oil, various surfactants, various oil fatty acids or their esters.

次に製剤例を示す。Examples of formulations are shown below.

製剤例１ 本発明化合物（１）〜（５５）の各々０．２部を各々白
灯油に溶解し、全体を１００部とすれば、各々の油剤を
得る。Formulation Example 1 By dissolving 0.2 parts of each of the compounds (1) to (55) of the present invention in white kerosene to make a total of 100 parts, each oil solution is obtained.

製剤例２ 本発明化合物（１）〜（５５）の各々１０部、それらに
、各々乳化剤【ツルポール８００５Ｘ（東邦化学登録商
標名））１５部、キシレン７５部を加え、これらをよく
攪拌混合すれば各々の乳剤を得る。Formulation Example 2 10 parts each of the compounds (1) to (55) of the present invention, 15 parts of an emulsifier [Turupol 8005X (registered trademark of Toho Chemical)], and 75 parts of xylene are added, and these are thoroughly stirred and mixed. Obtain each emulsion.

製剤例８ 本発明化合物（４０）　０．１部、テトラメスリン０．
２部、キシレン７部、脱臭灯油８２，７部を混合溶解し
、エアゾール容器に充填し、バルブ部分を取り付けた後
、該バルブ部分を通じて噴射剤（液化石油刀ス）６０部
を加圧充填４こにプ？γパ−ル１ングＪ。Formulation Example 8 0.1 part of the compound of the present invention (40), 0.1 part of tetramethrin.
After mixing and dissolving 2 parts of xylene, 7 parts of xylene, and 82.7 parts of deodorized kerosene, filling it into an aerosol container and attaching a valve part, 60 parts of a propellant (liquefied petroleum gas) was pressurized and filled through the valve part. Konipu? γ pearl 1 ng J.

製剤例４ 本発明化合物（４１）　０．１部、アレスリンのｄ−ト
ランス酸体０．２部、脱臭灯油１３．７部とｆｌＡｔｓ
Ｍ（アトモス３００（アトラスケミカル社登録商標名）
）１部とを混合し、純水５０部を加えて乳化させたのち
脱臭ブタン、脱臭プロパンの３部１混合物３５部ととも
にエアゾール容器に充填すればウォーター・ベースエア
ゾールを得る。Formulation Example 4 0.1 part of the compound of the present invention (41), 0.2 parts of d-trans acid form of allethrin, 13.7 parts of deodorized kerosene, and flAts
M (Atmos 300 (registered trademark name of Atlas Chemical Company)
), 50 parts of pure water is added to emulsify the mixture, and the mixture is filled into an aerosol container with 35 parts of a 3-part mixture of deodorized butane and deodorized propane to obtain a water-based aerosol.

製剤例５ 本発明化合物（４２）　０．８９に各々アレスリンのｄ
−トランス第一菊酸エステル０８ｆを加えメタノール２
０ｍ１ｔζ浴解し、蚊取線香担体（タブ粉：粕粉：木粉
をｇ：５：ｔの割合で混合）９９．４１１と均一に攪拌
混合し、メタノールを蒸散させた後、水１５０　ｍｅを
加え充分練り合せたものを成型乾燥すれば各々の蚊取線
香を得る。Formulation Example 5 The compound of the present invention (42) 0.89 and d of allethrin, respectively.
- Add trans primary chrysanthemum acid ester 08f and methanol 2
0 ml 1 t ζ bath dissolved, uniformly stirred and mixed with mosquito coil carrier (Tab powder: lees flour: wood flour mixed in the ratio of g: 5: t) with stirring, and after evaporating methanol, 150 me of water was added. Each type of mosquito coil is obtained by thoroughly kneading the mixture and molding and drying it.

製剤例６ 本発明化合物（１）、（４）、（７）、（８）の各々２
０部にフェニトロチオン１０部を加え、乳化剤（ツルプ
ール５０２９−０　（東邦化学登録商標名））５部をよ
く混合し、３００メツシュ珪藻土６５部を加え捕潰器中
にて充分攪拌混合すれば各々の水和剤を得る。Formulation Example 6 2 of each of the compounds (1), (4), (7), and (8) of the present invention
Add 10 parts of fenitrothion to 0 parts, mix well with 5 parts of emulsifier (Tsurpur 5029-0 (registered trademark of Toho Chemical)), add 65 parts of 300 mesh diatomaceous earth, and stir and mix thoroughly in a crusher. Obtain a hydrating powder.

製剤例７ 本発明化合物（１８）　、　（２１）　、　（２８）の
各々１部に各々ｌ−ナフチル−Ｎ−メチルカーバメート
２部を加え、適当量のアセトンに溶解し、８００メソシ
ュタルク９７部を加え、捕潰器中にて充分攪拌混合した
後、アセトンを蒸発除去すれば各々の粉剤を得る。Formulation Example 7 2 parts of l-naphthyl-N-methylcarbamate were added to 1 part each of the compounds of the present invention (18), (21), and (28), dissolved in an appropriate amount of acetone, and 97 parts of 800 mesostarc were added. In addition, after thorough stirring and mixing in a crusher, acetone is removed by evaporation to obtain each powder.

製剤例８ 本発明化合物（４４）、（４５）の各々５部に各々トヨ
リクニンＣＴ（東洋紡登録商標名）５部と（ｉ　Ｓ　Ｍ
クレー（ジークライト砿業登録商標名）９０部を加え、
拙潰器中にて充分に攪拌混合する。Formulation Example 8 5 parts each of the compounds (44) and (45) of the present invention, 5 parts each of Toyorikunin CT (Toyobo registered trademark) and (i S M
Adding 90 parts of clay (registered trademark name of Sieglite Milling Industry),
Thoroughly stir and mix in a crusher.

ついで水をこれら混合物の１０％量加え、さらに攪拌混
合して造粒機によって製粒し、通風乾燥すれば各々の粒
剤を得る。Next, 10% of water is added to the mixture, and the mixture is stirred and mixed, granulated using a granulator, and dried through ventilation to obtain each granule.

本発明化合物は広く農園芸用殺虫、殺ダニ剤として水田
、畑、果樹園、茶園、桑園、芝生地、牧草地、森林等で
使用できるほか防疫用殺虫、殺ダニ剤として用いること
もできる。The compounds of the present invention can be widely used as agricultural and horticultural insecticides and acaricides in rice paddies, fields, orchards, tea gardens, mulberry gardens, lawns, pastures, forests, etc., and can also be used as insecticides and acaricides for epidemic prevention.

次に本発明化合物が殺虫、殺ダニ剤の有効成分として有
用であることを試験例をあげて示す。Next, test examples will be given to demonstrate that the compounds of the present invention are useful as active ingredients for insecticides and acaricides.

本発明化合物は第１表の化合物番号で、また比較対照と
して用いた化合物は次の化合物記号でそれぞれ示す。The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used as comparative controls are indicated by the following compound symbols.

化合物記号　　　　構　造　式　　　　　　　備　考Ｍ
ｓ ＣＪｉ２（ＸＸＪＧ２Ｈ５ 試験例１ 製剤例２によって得られた下記本発明化合物の乳剤の水
による２００倍稀釈液（５００ｐｐｍ　相当）　２−を
１８１１のハスモンヨトウ用人工餌料にしみこませ、直
径１１ｃｒｎのポリエチレンカップに入れる。その中に
ハスモンヨトウ４令幼虫を１０頭放ち、６日後に生死を
調査した（２反復）。Compound symbol Structural formula Remarks M
s CJi2 (XXJG2H5 Test Example 1 A 200-fold dilution (equivalent to 500 ppm) of the emulsion of the compound of the present invention below obtained in Formulation Example 2 with water was impregnated into 1811 artificial feed for Spodoptera spp. and placed in a polyethylene cup with a diameter of 11 crn. Ten 4th instar larvae of Spodoptera were released into the larvae, and 6 days later, their survival and death were examined (2 repetitions).

試験例２ 製剤例２に準じて調製した　−Ｆ配本発明化合物の乳剤
の水による２００倍稀釈ｉ’ｌｆｆ（５００ｐｐｍ相当
）　１　ｍｌを直径５．５　ｃｍのポリエチレンカップ
内に調整したニカメイチュウ用人工飼料５ｆ中にしみこ
ませる。その中にニカメイガ１０日令幼虫ｌＯ頭を放ち
、８日後に生死を調査した（２反復）。その結果を下表
に示す。Test Example 2 Artificial feed for Japanese silverfish prepared in a polyethylene cup with a diameter of 5.5 cm containing 1 ml of i'lff (equivalent to 500 ppm) diluted 200 times with water of an emulsion of the -F compound of the present invention prepared according to Formulation Example 2. Let it soak into 5f. Into this, 10 10-day-old larvae of the Japanese corn borer were released, and after 8 days, the survival and death of the larvae was examined (2 repetitions). The results are shown in the table below.

試験例３ 製剤例２によって得られた下記本発明化合物および対照
化合物の乳剤の水による所定濃度の稀釈液にイネ基（見
さ約１０　ｃｍ　）を１分間浸漬する。風乾後、試験管
にイネ基を入れ抵抗性系統のツマグロヨコ）＜イ成虫を
１０頭放ち、１日後に生死を調査し、ＬＣａｏ値（５０
％致死濃度）を求めた（２反復）。Test Example 3 A rice plant (approximately 10 cm 2 in diameter) is immersed for 1 minute in a water dilution of the emulsion of the present invention compound and control compound obtained in Formulation Example 2 at a predetermined concentration. After air-drying, rice was placed in a test tube and 10 adult rice resistant strains were released. After 1 day, the survival and death were investigated and the LCao value (50
%lethal concentration) was determined (two replicates).

試験例４ 播種７日後の鉢植ツルナシインゲン（初生葉期）に、−
葉当り１０頭のニセナミハダニの雌成虫を寄生させ、２
５°Ｃの恒温室で保管する。６日後、製剤例２に準じて
ｍ整した下記本発明化合物および対照化合物の乳剤を水
で有効成分５００　ｐｐｍに希釈した薬液をターンテー
ブル上で１鉢あたり１０ｒｎｔ散布し、同時に同波２−
を土壌潅注する。８日後にそれぞれの植物のハダニによ
る被害を調査した。Test Example 4 7 days after sowing, -
10 adult female spider mites per leaf, 2
Store in a constant temperature room at 5°C. After 6 days, a drug solution prepared by diluting the following emulsion of the present compound and a control compound with water to 500 ppm of active ingredient was prepared according to Formulation Example 2, and was sprayed on a turntable at 10 rnt per pot, and at the same time, the same wave 2-
Irrigate the soil. Eight days later, each plant was examined for damage caused by spider mites.

効果判定基準は とした。その結果を下表に示す。The criteria for determining effectiveness is And so. The results are shown in the table below.

第１頁の続き ■Ｉｎｔ、　Ｃ１，３識別記号　　　庁内整理番号Ｃ０
７Ｃ１２１／７５　　　　　　　　　　　６４６４−４
Ｈ４８１００ ０発　明　者　矢野俊彦 宝塚市高司４丁目２番１号住友 化学工業株式会社内 ０発　明　者　平野維新 宝塚市高司４丁目２番１号住友 化学工業株式会社内Continuing from page 1 ■Int, C1, 3 identification code Office serial number C0
7C121/75 6464-4
H48100 0 Author: Toshihiko Yano, 4-2-1 Takashi, Takarazuka City, Sumitomo Chemical Co., Ltd. 0 Author: Hirano Ishin, 4-2-1 Takashi, Takarazuka City, Sumitomo Chemical Co., Ltd.

Claims (1)

【特許請求の範囲】 （１）　　一般式 〔式中、Ｒ＋およびＲ２は同一または相異なり、水素原
子、ハロゲン原子、低級アルキル基、低級アルコキシル
基、低級ハロアルキル基、低級ハロアルコキシル基、低
級アルキルチオ基、ニトリル基またはニトロ基を表わし
、さらに、Ｒ１とＲ２とが末端で結合し、１〜２個の酸
素原子または硫黄原子を環内に含んでいてもよい飽和ま
たは不飽和の５員環もしくは６員環を形成することもで
きる。 Ｒ８およびＲ４は同一または相異なり、メチル基または
エチル基を表わすかまたはＲｇとＲ４が末端で結合しエ
チレン基を表わす。 Ｘは酸素原子またはメチレン基を表わし、Ｙは、式 または一般式 で示される基（ここで、Ｒ５は水素原子またはフッ素原
子を表わし、ＩＬ６は水素原子、ハロゲン原子または低
級アルキル基を表わす。 Ｑは　窒素原子またはメチン基を表わし、２は酸素原子
、硫黄原子、イミノ基またはメチレン基を表わす。）を
表わす。〕 で示されるエーテル誘導体。 （２）一般式 〔式中、Ｒ１およびＲ２は同一または相異なり、水素原
子、ハロゲン原子、低級アルキル基、低級アルコキシル
基、低級ハロアルキル基、低級ハロアルコキシルＸ、　
低級アルキルチオ基、ニトリル基またはニトロ基を表わ
し、さらに、Ｒ１とＲ２とが末端で結合し、１〜２個の
酸素原子または硫黄原子を環内に含んでいてもよい飽和
または不飽和の５員環もしくは６貝環を形成することも
できる。 Ｒ８およびＲ４は同一または相異なり、メチル基または
エチル基を表わすか、または損とＲ４が末端で結合しエ
チレン基を表わし、Ｘは酸素原子またはメチレン基を表
わす。〕 で示されるアルコール化合物と一般式 ％式％ 〔式中、Ｙは式 または一般式 で示される基（ここで、Ｒ６は水素原子またはフッ素原
子を表わし、Ｒ６は水素原子、〕１０ゲン原子または低
級アルキル基を表わす。 Ｑは窒素原子またはメチン基を表わし、２は酸素原子、
硫黄原子、イミノ基またはメチレン基を表わす。）を表
わす。］ Ａ１はハロゲン原子、トシルオキシ基またはメシルオキ
シ基を表わす。］ で示される化合物とを、脱酸剤の存在下に反応させるこ
とを特徴とする一般式 〔式中、Ｒ１，Ｒ２，Ｒ１１，Ｒ４，ＸおよびＹは前述
と同じ意味を表わす。〕 で示されるエーテル誘導体の製造法。 （８）　　一般式 〔式中、Ｒ１および街は同一または相異なり、水素原子
、ハロゲン原子、低級アルキルｉ、ａａアルコキシル基
、低級ハロアルキル基、低級ハロアルコキシル基、低級
アルキルチオ基、ニトリル基またはニトロ基を表わし、
さらにｌｉｔとＲ２とが末端で結合し、１〜２ａの酸素
原子または硫黄原子を環内に含んでいてもよい飽和また
は不飽和の５員環もしくは６員環を形成することもでき
る。 Ｒ３およびＲ４は同一または相異なり、メチル基または
エチル基を表わすかまたはＲ８とＩＬａが末端で結合し
エチレン基を表わす。 Ｘは酸素原子または　メチレン基を表わし、Ａ２はハロ
ゲン原子、トシルオキシ基またはメシルオキシ基を表わ
す。〕 で示される化合物と一般式 ％式％ 〔式中、Ｙは式 または一般式 で示される基（ここで、Ｒ５は水素原子またはフッ素原
子を表わし、Ｒ６は水素原子、ノーロゲン原子または低
級アルキル基を表わす。 Ｑは窒素原子またはメチン基を表わし、２は酸素原子、
硫黄原子、イミノ基またはメチレン基を表わす。）を表
オ）す。］ で示されるアルコール化合物とを、脱酸剤の存在下に反
応させることを特徴とする一般式〔式中、几１．　Ｒ２
、Ｒｓ　、　Ｒ４、ＸおよびＹは前述と同じ意味を表わ
す。〕 で示されるエーテル誘導体の製造法。 （４）　　一般式 〔式中、Ｒ１および几２は同一または相異なり、水素原
子、ハロゲン原子、低級アルキル基、低級アルコキシル
ｘ、低級ハロアルキル基、低級ハロアルコキンル基、低
級アルキルチオ基、ニトリル基またはニトロ基を表オ）
し、さらに、■も１とＲ２とが末端で結合し、１〜２個
の酸素原子または硫黄原子を環内に含んでいてもよい飽
和または不飽和の５員環もしくは６員環を形成すること
もてきる。］ で示されるフェノール誘導体と一般式 ％式％ 〔式中、Ｒｇおよび、Ｌは同一または相異なり、メチル
基またはエチル基を表わすかまたは損とＥ、４が末端で
結合しエチレン基を表わす。 Ｙは　式 または一般式 で示される基（ここで、１員は水素原子またはフッ素原
子を表わし、Ｒ６は水素原子、７１０ゲン原子または低
級アルキル基を表イ）す。 Ｑは　窒素原子またはメチン基を表わし、２は酸素原子
、硫黄原子、イミノ基またはメチレン基を表わす。）を
表わす。 Ａａ　ハロゲン原子、トシルオキシ基またはメシルオキ
シ基を表わす。］ で示される化合物とを、脱酸剤の存在下に反応させるこ
とを特徴とする一般式 〔式中、Ｒ１、Ｒ２、Ｒａ　、几４およびＹは前述と同
じ意味を表わす。〕 で示されるエーテル誘導体の製造法。 （５）一般式 〔式中、Ｂ、１および１１２は同一または相異なり、水
素原子、ハロゲン原子、低級アルキルＡＥ、　、低級ア
ルコキシル基、低級ハロアルキル基、に９ハロアルコキ
シル基、　低級アルキルチオ基、ニトリル基ｆ、　ｆこ
はニトロ基を表わ【７、さらに、石と１ｌＬ２とが末端
で結合し、１〜２個の酸素原子または硫黄原子を環内に
含んでいてもよい飽和または不飽和の５員環もしくは６
員環を形成することもできる。 Ｒ３および山は同一または相異なり、メチル基またはエ
チル基を表わすか、または拘とＲａが末端で結合しエチ
レン基を表わす。 Ｘは酸素原子または　メチレン基を表わし、Ｙは　式 または一般式 で示される基（ここで、Ｒ５は水素原子またはフッ素原
子を表わし、Ｒ６は水素原子、７１０ゲン原子または低
級アルキル基を表わす。 Ｑは窒素原子またはメチン基を表オ）し、２は酸素原子
、硫黄原子、イミノ基またはメチレン基を表わす。）で
示される基を表わす。】 で示されるエーテル誘導体を有効成分として含有するこ
とを特徴とする殺虫、殺ダニ剤。[Scope of Claims] (1) General formula [wherein R+ and R2 are the same or different, hydrogen atom, halogen atom, lower alkyl group, lower alkoxyl group, lower haloalkyl group, lower haloalkoxyl group, lower alkylthio group , represents a nitrile group or a nitro group, and furthermore, R1 and R2 are bonded at the terminal, and a saturated or unsaturated 5-membered ring or a 6-membered ring which may contain 1 to 2 oxygen atoms or sulfur atoms in the ring. It is also possible to form a membered ring. R8 and R4 are the same or different and represent a methyl group or an ethyl group, or Rg and R4 bond at the terminal to represent an ethylene group. X represents an oxygen atom or a methylene group, and Y represents a group represented by the formula or general formula (wherein, R5 represents a hydrogen atom or a fluorine atom, and IL6 represents a hydrogen atom, a halogen atom, or a lower alkyl group. Q represents a nitrogen atom or a methine group, and 2 represents an oxygen atom, a sulfur atom, an imino group or a methylene group. ] An ether derivative represented by (2) General formula [wherein R1 and R2 are the same or different, hydrogen atom, halogen atom, lower alkyl group, lower alkoxyl group, lower haloalkyl group, lower haloalkoxyl X,
A saturated or unsaturated 5-membered ring which represents a lower alkylthio group, a nitrile group or a nitro group, and in which R1 and R2 are bonded at the terminal, and which may contain 1 to 2 oxygen atoms or sulfur atoms in the ring. It is also possible to form a ring or a six-shell ring. R8 and R4 are the same or different and represent a methyl group or an ethyl group, or a terminal bond between R8 and R4 represents an ethylene group, and X represents an oxygen atom or a methylene group. [In the formula, Y is a group represented by the formula or the general formula (here, R6 represents a hydrogen atom or a fluorine atom, R6 is a hydrogen atom,] 10 gene atoms or Represents a lower alkyl group. Q represents a nitrogen atom or a methine group, 2 represents an oxygen atom,
Represents a sulfur atom, imino group or methylene group. ). ] A1 represents a halogen atom, a tosyloxy group or a mesyloxy group. [In the formula, R1, R2, R11, R4, X and Y have the same meanings as above. ] A method for producing an ether derivative shown in (8) General formula [wherein R1 and groups are the same or different, hydrogen atom, halogen atom, lower alkyl i, aa alkoxyl group, lower haloalkyl group, lower haloalkoxyl group, lower alkylthio group, nitrile group, or nitro group represents,
Furthermore, lit and R2 can be bonded at the terminals to form a saturated or unsaturated 5- or 6-membered ring which may contain 1 to 2a oxygen atoms or sulfur atoms in the ring. R3 and R4 are the same or different and represent a methyl group or an ethyl group, or R8 and ILa are bonded at the terminal to represent an ethylene group. X represents an oxygen atom or a methylene group, and A2 represents a halogen atom, a tosyloxy group or a mesyloxy group. ] Compounds represented by the general formula % formula % [wherein, Y is the formula or a group represented by the general formula (where R5 represents a hydrogen atom or a fluorine atom, and R6 represents a hydrogen atom, a norogen atom or a lower alkyl group] Q represents a nitrogen atom or a methine group, 2 represents an oxygen atom,
Represents a sulfur atom, imino group or methylene group. ). ] A general formula characterized by reacting an alcohol compound represented by the following in the presence of a deoxidizing agent [wherein 几1. R2
, Rs, R4, X and Y have the same meanings as above. ] A method for producing an ether derivative shown in (4) General formula [wherein R1 and 几2 are the same or different, hydrogen atom, halogen atom, lower alkyl group, lower alkoxyl x, lower haloalkyl group, lower haloalcokynyl group, lower alkylthio group, nitrile group, or nitro group )
In addition, (1) and R2 are bonded at the terminal to form a saturated or unsaturated 5- or 6-membered ring which may contain 1 to 2 oxygen atoms or sulfur atoms in the ring. It can also happen. ] Phenol derivatives represented by the general formula % [wherein Rg and L are the same or different and represent a methyl group or an ethyl group, or Rg, E, and 4 are bonded at the terminal to represent an ethylene group. Y is a group represented by the formula or the general formula (wherein, one member represents a hydrogen atom or a fluorine atom, and R6 represents a hydrogen atom, a hydrogen atom, or a lower alkyl group). Q represents a nitrogen atom or a methine group, and 2 represents an oxygen atom, a sulfur atom, an imino group or a methylene group. ). Aa represents a halogen atom, tosyloxy group or mesyloxy group. [In the formula, R1, R2, Ra, 4 and Y have the same meanings as above. ] A method for producing an ether derivative shown in (5) General formula [wherein B, 1 and 112 are the same or different, hydrogen atom, halogen atom, lower alkyl AE, lower alkoxyl group, lower haloalkyl group, 9-haloalkoxyl group, lower alkylthio group, nitrile The group f, f represents a nitro group [7, and furthermore, a saturated or unsaturated group in which the stone and 1L2 are bonded at the terminal and which may contain 1 to 2 oxygen atoms or sulfur atoms in the ring. 5-membered ring or 6-membered ring
It is also possible to form a membered ring. R3 and M are the same or different and represent a methyl group or an ethyl group, or R3 and Ra are bonded at the terminal to represent an ethylene group. X represents an oxygen atom or a methylene group, and Y represents a group represented by the formula or the general formula (wherein, R5 represents a hydrogen atom or a fluorine atom, and R6 represents a hydrogen atom, a gen atom, or a lower alkyl group. represents a nitrogen atom or a methine group, and 2 represents an oxygen atom, a sulfur atom, an imino group or a methylene group. ) represents a group represented by ] An insecticide and acaricide characterized by containing an ether derivative represented by the following as an active ingredient.
JP58101245A 1983-06-06 1983-06-06 Ether derivative, its preparation, and insecticide and acaricide comprising it as active ingredient Granted JPS59225135A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP58101245A JPS59225135A (en) 1983-06-06 1983-06-06 Ether derivative, its preparation, and insecticide and acaricide comprising it as active ingredient

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP58101245A JPS59225135A (en) 1983-06-06 1983-06-06 Ether derivative, its preparation, and insecticide and acaricide comprising it as active ingredient

Publications (2)

Publication Number Publication Date
JPS59225135A true JPS59225135A (en) 1984-12-18
JPH042578B2 JPH042578B2 (en) 1992-01-20

Family

ID=14295517

Family Applications (1)

Application Number Title Priority Date Filing Date
JP58101245A Granted JPS59225135A (en) 1983-06-06 1983-06-06 Ether derivative, its preparation, and insecticide and acaricide comprising it as active ingredient

Country Status (1)

Country Link
JP (1) JPS59225135A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986001501A1 (en) * 1984-08-30 1986-03-13 Commonwealth Scientific And Industrial Research Or Arthropodicides
EP0220810A1 (en) * 1985-09-23 1987-05-06 Imperial Chemical Industries Plc Insecticidal ethers

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986001501A1 (en) * 1984-08-30 1986-03-13 Commonwealth Scientific And Industrial Research Or Arthropodicides
EP0220810A1 (en) * 1985-09-23 1987-05-06 Imperial Chemical Industries Plc Insecticidal ethers
US4705900A (en) * 1985-09-23 1987-11-10 Imperial Chemical Industries Plc Insecticidal alkenes
AP28A (en) * 1985-09-23 1988-12-20 Ici Plc Insecticidal alkenes.

Also Published As

Publication number Publication date
JPH042578B2 (en) 1992-01-20

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